3-Nitrosalicylic acid → Benzyl 2-(benzyloxy)-3-nitrobenzoate

HRID 1064840Notes

Reaction equation

HRID 1064840 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]=1[OH:19])([O-:9])=[O:8].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[CH2:20]([O:19][C:11]1[C:10]([N+:7]([O-:9])=[O:8])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH2:13][C:12]1[CH:16]=[CH:17][CH:18]=[CH:10][CH:11]=1)=[O:14])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 68073-Nitrosalicylic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 16106676Benzyl 2-(benzyloxy)-3-nitrobenzoateYield 162.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (16.6 g, 120.1 mmol) was added to a solution of 3-nitrosalicylic acid (10 g, 54.6 mmol) in DMF (100 ml) and benzyl bromide (14.3 ml, 120.1 mmol) was dropped thereinto. The mixture was stirred at 80° C. for 12 hours and the reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and the solvent was evaporated therefrom to provide 16.1 g (yield 81%) of benzyl 2-benzyloxy-3-nitrobenzoate as brown oil.

Workup

  1. additionwas dropped
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-76696d917e2a459a86cc68998cf3ba90
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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